Water → 6,7-Dimethyl-5-methoxy-1,3-dihydro-2H-indole-2-one

HRID 1743397Notes

Reaction equation

HRID 1743397 reaction equation
[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH:6](SC)[C:7](=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:15][CH3:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.O>ClCCl>[CH3:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7](=[O:12])[NH:8]2)=[CH:4][C:3]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 222380776,7-Dimethyl-5-methoxy-3-(methylthio)-1,3-dihydro-2H-indole-2-one

Product 1

HCID 222380866,7-Dimethyl-5-methoxy-1,3-dihydro-2H-indole-2-oneYield 72.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dimethyl-5-methoxy-3(methylthio)-1,3-dihydro-2H-indole-2-one (30 g, 126 mmol) in dichloromethane (600 mL) were added triphenylphosphine (40 g, 153 mmol) and toluenesulfonic acid monohydrate (29 g, 153 mmol) at room temperature, and the mixture was stirred for 3 hours. The reaction solution was poured into cool water, and the precipitated crystals were filtered. The crystals were washed with dichloromethane and water to obtain 17.5 g of the title compound.

Workup

  1. additionThe reaction solution was poured
  2. filtrationthe precipitated crystals were filtered
  3. washThe crystals were washed with dichloromethane and water

Sources & evidence

ORD record
ord-ad8c36e386b34d36a1b6ea7ae5f1c0fb
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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